First Time Milking
Date: 07.03.2010
Keywords: Milking, First, Time,
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I had not seen Linds in a while. She stopped by with her friend Joan. I had never seen Joan before. She was beautiful, long brown hair and long slender shapely legs to match. They both wore short skirts that hugged their figure. They stopped by to pay a visit and check up on me. I quickly found out the real reason for their visit. They wanted to know if they could have a party at my place and to invite a few friends from college and the local area. I really did not have a problem with that but played like I did. And of course Linds knew just how to sway me over to her way of thinking.
Linds got that look in her eyes that I know so well, and Joan smiled wickedly at me and turned to Linds saying, "Well, I guess we will have to convince him somehow."
Linds giggled, "Hmmm, it has been a while since I had him between my feet and toes. Maybe that would work." I looked at her feet. She wore pumps and her high arches looked so inviting.
I laughed, "Ladies, that would definitely put me in the right frame of mind."
They both laughed and Linds said, "To the bedroom then!" We made our way up the stairs making sure I positioned myself behind them. Joan was directly in front of me and I had a great vantage point of her tight ass and shapely calves.
Joan looked over her shoulder at me and smiled.
Linds commented, "Joan, you have to try that milking thing out on Mr. C."
We made our way into my bedroom and Linds said, "Only if he wants to."
I sat on the bed removing my clothes and asked them, "What is this milking thing you two are talking about?"
Linds said, "It is something Joan has been doing with her boyfriend. I will let her explain it to you."
I had gotten over feeling uncomfortable in the nude in Linds presence. However, being naked in front of Joan, whom I just met, made me feel a bit uneasy.
I stretched out on the bed and Joan smiled saying, "Mmmmm, Linds you were right, for a 40 year old man he does not have a bad looking body."
This put me more at ease with her. I watched as they both slipped off their shoes. Joan's feet looked amazing. Linds was wearing pumps and Joan had on a pair of black mules.
Linds sat on the bed cross-legged next to my right hip. She pulled her long hair back over her shoulders and then grabbed my already hard cock and began to fondle it.
Linds approached the foot of the bed saying to me, "Make room for me and spread your legs please."
I did as she instructed and watched as she took a seat on the bed between my legs. She also sat crossed-legged. Her legs were amazingly long and shapely. Her calves were smooth and nicely formed. She lifted each of my legs up and rested them on top of her crossed thighs. With my legs raised atop her thighs she was able to scoot in closer to me between them. Linds continued to stroke my shaft causing me to moan. She leaned over me, her beautiful face hovering over mine smiling as she said, "I love the way you feel in my hands."
Joan said, "Let me." And reached over grabbing my cock. Linds released me and leaned over to the bedside stand and pulled out the bottle of baby oil from the drawer. She applied a generous amount over my cock and Joan's stroking hand. Joan's fingers were slender and much longer than Linds and wrapped completely around my throbbing shaft.
As Linds applied a liberal amount of oil Joan smiled saying, "That's better, I like the slippery feel and smacking sound a cock makes in my hand."
After a few more strokes she stopped stroking my shaft and began to rub her long thumb very slowly up and down along the sensitive glands at the head of my cock. She finished each slow torturous thumb rub by squeezing the head of my cock firmly. Her doing this to me caused my body to tense up and raise my hips into the air. She saw what her thumb rubbing was doing to me and smiled. Linds saw this and reached in with her left hand grabbing the shaft of my cock between her fingers and stroked it while Joan continued to relentlessly rub and squeeze my sensitive head.
Linds said, "He likes it when you do that with your thumb."
Joan replied, "I can see that. His body is really tense."
I moaned each time Joan's thumb passed over my cock's swollen head. She was relentless as was Linds who continued to pump my shaft. It did not take long before I started to ooze precum. I watched as it leaked out of my slit and on to Joan's thumb.
Joan giggled saying, "There it is. Amazing what my thumb can do."
Linds said, "His cock is throbbing in my hand."
Joan said, "That's a good sign."
Linds and Joan stopped what they were doing and Joan began to fondle my balls as she explained to me about how she wanted to milk me. She explained that she would insert her finger up my ass pumping it against my prostrate. All the while keeping me hard. She said it would allow me to remain hard much longer and my orgasm would be much more intense and longer.
After explaining all this to me I was pretty sure it was not for me. I said, "I do not like anything stuck up my ass. I prefer to remain a virgin there."
Linds laughed, "Oh c'mon just try it once. I will keep playing with your cock while she does it."
Joan said, "It will not hurt you. I have done this many times to Ron, my boyfriend, and he says it is so intense. I know what I am doing and I promise to be gentle."
They both continued to talk to me about it trying to convince me. Joan kept playing with my balls. I watched as her slender fingers worked their magic. Finally after much deliberation I agreed. I further explained that the moment I said stop they would have to stop. They agreed.
Joan slid my legs off of hers and got up from the bed. She made her way over to where she had placed her purse and brought back with her a small jar of KY jelly. I commented, "Do you always carry that with you."
She smiled at me saying, "I never leave home without it."
She assumed her position between my legs, only this time scooted herself in even closer causing my hips to spread even wider and my buttocks to tilt up higher towards her.
Linds looked on and asked Joan what should she do?
Joan told her to get me to the point of precum again while she does her thing.
Linds immediately placed her foot in my lap and inserted my cock in between her big toe and second toe. She began to jerk my cock the length of my shaft all the way up to the head where she paused and gently wiggled her toes back and forth a few times then stroked me again. It was driving me crazy and she knew it. I fit very tightly between her toes.
Joan said, "I can tell u have done this before." She poked her finger in the jar and pulled out a healthy dollop of KY.
Linds said, "It shouldn't take too long before he starts oozing. I just have to work his head between my toes."
Her toes were working me over good. I began moving my hips up and down and my moans of pleasure were coming more frequently.
Linds raised up her other leg and laid it across my lower abdomen pressing it against the shaft of my cock propping it upright. The sight and weight of her smooth shapely calf across my abdomen excited me further.
Joan reach down between my butt cheeks and I felt her gently separate them she lowered her face down a bit to get a better view. She smiled at me and said, "Nice virgin bud you have there. Now you have to relax and let my finger slide in. Do not tighten it up. I promise it won't hurt."
I felt her apply the lube against my rectum and then she gently entered her finger up to the first digit. I could not help but tighten my muscles. She smiled at me and said, "Relax now, I am going to move it around a bit so you get use to my finger." Linds continued to stroke me between her toes as I felt Joan's finger moving up down and around inside me. After a while I felt her finger enter me further. I asked, "Is that it?"
Joan laughed, "Oh no. Only half way, I still got more to go sweetie. I can feel your muscles contracting around my finger. You have to relax and accept me." Then she smiled at me and said, "I love pumping my fingers inside a virgin. At this moment you probably feel a sensation of being violated. That's okay, the feeling of being violated is normal, don't worry after a while the feeling will go away. You and I are going to be real close." Her smile broadened even wider as she pushed her finger in even further.
I said, "I am trying to relax but God u have long fingers!"
They both laughed and Joan said, "That's funny…Ron tells me the same thing." She then added, "I am going to move it around again so you get use to it."
I began to breath harder and Linds asked, "How you doing sweetie? Does it feel okay?"
All I could do was grunt and take short breaths.
I tried to take my mind off of what Joan was doing to me as I concentrated on Lind's golden toes working over my cock. I could not help but move my hips up and down. She applied more oil to her toes and reached down with a free hand to stroke my shaft while her toes began to squeeze and work harder on the sensitive area of my head.
Joan concentrated on what she was doing to me as I felt her finger move even further inside me. She said, "almost there now."
I gasped, "Thank goodness."
Linds commented on how my cock was throbbing and twitching.
Joan said, "That's good he is responding to what I am doing to him."
Linds said excitedly, "There it is, he is starting to precum now."
I looked at Linds toes and saw beads of my precum ooze out of my slit and onto her beautiful toes.
Suddenly I felt Joan's finger slip in further and press against what had to be my prostrate. I arched my back up and groaned loudly, "Oh God!"
Joan said, "That's it I am all the way in now. See how he responded Linds?" Linds laughed, "Hell yes! He bucked so high my knee almost rammed into my chin."
Joan bent her head down further to examine what she was doing to me saying, " I just poked something inside him never touched before."
Linds said, " That's so wonderful."
I relaxed a bit then Joan moved the tip of her finger back and forth against my prostrate.
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Keywords: Milking, First, Time,